反应详情

In a 100 mL three-neck round bottom flask under a nitrogen atmosphere and with magnetic stirring, a solution of 1.0 g (4.8 mmol) of 4-chloro-6-methoxy-2-methylquinoline and 10 mL of n-octylamine was heated under reflux for three hours. Upon cooling to room temperature, the reaction mixture formed a glassy solid which was filtered. This was triturated under isopropyl ether filtered and washed with additional ether. The solid was stirred with a mixture of water and ethyl acetate; insolubles were filtered and discarded; the ethyl acetate layer eventually furnished 500 mg of 6-methoxy-2-methyl-N-octylquinolin-4-amine hydrochloride: m.p. 178°-179° C. Without further purification, a solution of 350 mg (1.04 mmol) of this material and 42 mL of 48% hydrobromic acid was heated reflux for 18 hours. Upon cooling, the reaction solution gave a precipitate which was filtered. The filtrate was evaporated to furnish a solid residue. The combined solids were recrystallized from hot water to give 45 mg (12%) of 2-methyl-4-octylaminoquinolin-6-ol hydrobromide hemihydrate: m.p. 176°-178° C.

1. temperatureunder reflux for three hours
2. customthe reaction mixture formed a glassy solid which
3. filtrationwas filtered
4. customThis was triturated under isopropyl ether
5. filtrationfiltered
6. washwashed with additional ether
7. filtrationinsolubles were filtered
8. customWithout further purification
9. temperaturereflux for 18 hours
10. temperatureUpon cooling
11. customthe reaction solution gave a precipitate which
12. filtrationwas filtered
13. customThe filtrate was evaporated
14. customto furnish a solid residue
15. customThe combined solids were recrystallized from hot water